Imidazole → 1H-Imidazole, 1-(2-naphthalenylmethyl)-

HRID 865989Notes

Reaction equation

HRID 865989 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1.O>C(Cl)Cl>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[CH2:7][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 703202-Bromomethylnaphthalene

Product 1

HCID 1865821H-Imidazole, 1-(2-naphthalenylmethyl)-Yield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of imidazole (15.4 g, 0.226 mol) and 2-bromomethylnaphthalene (22 g, 0.0995 mol) in 200 ml of methylene chloride was stirred at room temperature overnight. The mixture was stirred with 200 ml of water, the organic layer was washed with water (2×200 ml), and stirred with 30 ml of conc. HCl and 200 ml of water. After filtration for the removal of the solid, the methylene chloride layer was discarded, and the aqueous layer was extracted with 200 ml of ether. The above aqueous layer was basified with 3N NaOH solution, extracted with methylene chloride, and the organic layer was dried over magnesium sulfate. The above organic solution was concentrated in vacuo to afford 13.65 g of 1-(2-naphthylmethyl)imidazole, m.p. 87°-88° C.

Workup

  1. washthe organic layer was washed with water (2×200 ml)
  2. stirringstirred with 30 ml of conc. HCl and 200 ml of water
  3. filtrationAfter filtration
  4. customfor the removal of the solid
  5. extractionthe aqueous layer was extracted with 200 ml of ether
  6. extractionextracted with methylene chloride
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. concentrationThe above organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f43e6c44fff649fba578cd5ea60d5f2f
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

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